Brian takes Andrew's anal virginity

The entrance now loosened and with ‘her’ high-heel clad legs resting on ‘her’ date’s shoulders, Andrea steeled herself for the main event, as Brian’s humongous and rock-hard phallus sprang out of his downed boxers.

Applying a lot of lube to both Andrea’s hole and his shaft, Brian asked “You ready?”, but before Andrea could even answer, he thrust his cock straight in to the base, causing ‘her’ to scream in agony.

This wasn’t the sweet low-key pain masked by mounting pleasure from earlier; this was true anguish, the likes of which Andrew had never felt before.

The pain only intensified at first as Brian began thrusting in and out, his massive bulk far too wide and long for Andrea’s tiny boi pussy, but gradually it acclimatised, and the pleasure finally emerged from the pain.

Andrea had **** but focus on that pleasure, letting it cement in ‘her’ mind and nurturing it like a horticulturist with a flower, and like a flower, it grew and grew, sapping away the strength of the surrounding pain to feed itself.

After twenty minutes, the pain and pleasure were on equal terms, and ten minutes after that, excitation had taken over and Andrea’s wails of pain had changed to moans of pleasure.

‘Oh fuck, this is so fucking disgusting, my best friend is fucking me in the ass, and I can’t help but fucking love it!’, Andrew thought as the flesh camber slammed against his prostate again and again.

When Brian angle himself so he was reaching over Andrea, ‘she’ couldn’t help but hold hands with him and stare deep into his eyes with lust as Brian continued to whittle away at his straightness and psyche, furiously making out with him missionary-style.

The sensations were too much, and Andrea found ‘herself’ experiencing another, more intense prostate orgasm.

Andrea wasn’t sure how, but Brian was able to keep on going without releasing his nut way longer than when ‘she’ gave him blowjobs or handjobs, despite being pretty sure from his grunts that he was in more sexual rapture than before.

Andrew would almost be impressed or proud for Brian were it not that his rational thought processing had completely gone out the window.

Andrea had become a cock-crazed whore in the heat of the moment, letting Brian switch positions at will and call her a “bitch”, “slut”, and a myriad of other insults, only caring about the bliss within ‘her’ mystery spot.

‘She’ even began riding Brian cowgirl style, bouncing up and down the pork sword like a pogo stick.

Finally in the doggy position, Brian excreted his load inside Andrea’s ass as ‘she’ had one last mind blowing anal orgasm, whatever cum leaking out her tuck being absorbed by her panty liner.

The two collapsed next to each other and made out for a little while, still in the grasp of euphoria, till they grew too tired and turned the lights off to go to sleep.

With the endorphins and hormones dissipated, reality came crashing down on Andrew like a bucket of icy water, leaving him drenched in a cold sweat and shivering as he tried to process what he had just done.

‘Brian… fucked me… in my ass… and I loved it… Jesus fucking Christ, why?...’.

Andrew’s mood was made even worse when Brian reasoned, “I guess this means we’re going steady, huh?”.

Andrew quietly cried himself to sleep in the bed of shame and self-hatred he had made, while Brian took the opportunity to take a picture of the cum leaking out of Andrea’s ass.

‘Awe man, Andrew’s gonna be so stoked when he hears about this!’.